Pyrazine-sulfonylcarbamates and thiocarbamates

ABSTRACT

The claimed invention is a pyrazine of the formula: ##STR1## where Z is oxygen or sulfur and R is C 1  -C 4  alkyl, phenyl or benzyl. The pyrazine ring may be variously further substituted. The above noted pyrazines are useful as intermediates in the production of herbicides.

This is a divisional of application Ser. No. 496,325, filed on May 19,1983, now U.S. Pat. No. 4,612,037.

The present invention relates to a group of novel sulfonylureas andsulfonylthioureas which have valuable growth regulating properties andwhich are suitable for selectively influencing plant growth, for thecontrol of weeds e.g. in crops of useful plants and/or for influencingthe phytotoxic properties of other herbicidal compounds. The inventionalso relates to the preparation of these sulfonylureas andsulfonylthioureas, and to agricultural compositions which contain them.

Accordingly, the invention relates to compounds of the formula I##STR2## wherein R₁ is hydrogen or C₁ -C₅ alkyl,

R₂ and R₃, each independently of the other, are hydrogen, C₁ -C₅ alkyl,C₁ -C₅ alkoxy, C₁ -C₅ alkylthio, C₁ -C₅ haloalkyl, halogen, C₁ -C₅haloalkylthio, C₁ -C₄ alkylamino, C₁ -C₄ dialkylamino, an alkoxyalkylgroup or alkoxyalkoxy group, each containing not more than 6 carbonatoms,

Z is oxygen or sulfur,

E is --CH═ or --N═, and

Q is an unsubstituted or substituted 6-membered heterocyclic radicalcontaining 2 to 3 nitrogen atoms and bound through a carbon atom, andthe salts thereof.

Depending on the indicated number of carbon atoms, alkyl by itself or asmoiety of another substituent will be understood as meaning e.g. thefollowing groups: methyl, ethyl, propyl, butyl or pentyl and the isomersthereof such as isopropyl, isobutyl, tert-butyl, isopentyl etc.Haloalkyl denotes a monohalogenated or perhalogenated alkyl radical,e.g. CF₃, CH₂ Cl, CCl₃, CHCl₂, CH₂ I, C₂ H₄ Cl, C₂ H₄ Br etc. Throughoutthis specification, halogen denotes fluorine, chlorine, bromine oriodine, with fluorine, chlorine or bromine being preferred.Agriculturally suitable salts are e.g. those which the compounds offormula I form with amines, alkaline metal bases or alkaline earth metalbases, or with quaternary ammonium bases. Suitable alkali metal oralkaline earth metal bases will be understood as meaning here inparticular the hydroxides, such as lithium, sodium, potassium, magnesiumor calcium hydroxide.

Examples of suitable salt-forming amines are primary, secondary andtertiary aliphatic and aromatic amines such as methylamine, ethylamine,propylamine, isopropylamine, the four butylamine isomers, dimethylamine,diethylamine, diethanolamine, dipropylamine, diisopropylamine,di-n-butylamine, pyrrolidine, piperidine, morpholine, trimethylamine,triethylamine, tripropylamine, quinuclidine, pyridine, quinoline andisoquinoline. Preferred amines are ethylamine, propylamine, diethylamineor triethylamine, with isopropylamine and diethanolamine being mostpreferred.

Examples of quaternary ammonium bases are, in general, the cations ofhaloammonium salts, e.g. the tetramethylammonium cation, thetrimethylbenzylammonium cation, the triethylbenzylammonium cation, thetetraethylammonium cation, the trimethylethylammonium cation, and alsothe ammonium cation.

Typical substituents of the radical Q in formula I are: halogen,pseudohalogen, nitro, alkyl, haloalkyl, alkoxy, alkylthio, haloalkoxy,haloalkylthio, amino, alkylamino, dialkylamino, alkylcarbonylamino,alkylcarbonyl, alkoxycarbonyl, alkylthiocarbonyl, carbamoyl,alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfinyl, alkylsulfonyl,alkenyloxy, alkynyloxy, and the following groups such as phenyl, phenoxyor phenylthio, which are unsubstituted or substituted by halogen, nitro,cyano, alkyl, alkoxy, haloalkyl or haloalkoxy, and also benzyl or benzylsubstituted by halogen and/or alkyl. Preferred substituents are thosecontaining not more than 6, preferably not more than 4, carbon atoms inthe aliphatic moiety.

The following 6-membered heterocyclic radicals Q are typicalsubstituents within the scope of this invention: pyrimidine, pyridazine,pyrazine and triazine, with pyrazine being preferred.

The heterocyclic radical Q may be unsubstituted or contain one or moresubstituents.

The compounds of formula I are biologically active oils, resins orsolids which are stable at room temperature and have very valuablegrowth regulating, in particular, growth inhibiting, properties. Theycan therefore be used in agriculture or related fields for selectivelyreducing the growth of monocot and dicot plants. Depending on the modeof application or on the rate of application, the compounds act asselective or total herbicides.

A preferred group of compounds of formula I comprises those compoundswherein Z is oxygen and R₁ is hydrogen.

A particularly preferred group of compounds of formula I comprises thosecompounds wherein R₁ is hydrogen, each of R₂ and R₃ independently of theother is C₁ -C₃ alkyl, C₁ -C₃ alkoxy, C₁ -C₃ haloalkyl, C₁ -C₃haloalkoxy, halogen or C₂ -C₄ alkoxyalkyl, Z is oxygen, E is nitrogen orCH, Q is a heterocyclic radical as defined for formula I which isunsubstituted or substituted by a member selected from chlorine,bromine, fluorine, nitro, cyano, C₁ -C₄ alkylcarbonyl, C₁ -C₄alkoxycarbonyl, C₁ -C₃ alkoxy, C₁ -C₃ alkylthio, C₃ -C₅ alkoxyalalkoxy,C₁ -C₃ -alkylsulfinyl, C₁ -C₃ alkylsulfonyl, C₁ -C₄ alkyl,trifluoromethyl, trichloromethyl, C₁ -C₄ cyanoalkyl, C₂ -C₄ alkenyloxy,C₃ -C₄ alkynyloxy or N--C₁ -C₄ alkylcarbonylamino.

Particularly preferred individual compounds are:

N-(2-methylpyrazin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaand

N-(2-methoxypyrazin-3-ylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.

The compounds of formula I may be prepared in a manner known per se inan inert organic solvent or mixture of solvents.

The compounds of formula I may be prepared as follows in accordance withequation [1] ##STR3## by reacting a phenylsulfonyl derivative of theformula II with a compound of the formula III, wherein X and W are--NH₂, --N═C═Z or --NR₁ --CZ--OR groups, the substituents R₁, R₂, R₃, Q,Z and E are as defined for formula I, R is an aliphatic or aromaticradical, preferably C₁ -C₄ alkyl, phenyl or benzyl, with the provisothat the reactants of the formulae II and III are also so chosen that anamino function reacts either with an isocyanato or isothiocyanatofunction or with the [--NR₁ --CZ--OR] group.

The process is conveniently carried out in the presence of a base. Itcan often be of advantage to carry out the reaction in an inert gasatmosphere, e.g. under nitrogen. The process for preparing the compoundsof formula I is an object of the invention.

If desired, the compounds of formula I may be converted into basic,agriculturally suitable addition salts by reaction with amines, alkalimetal hydroxides or alkaline earth metal hydroxides, or with quaternaryammonium bases. This is accomplished e.g. by reacting a compound offormula I with an equimolar amount of base and removing the solvent byevaporation. Such reactions, and also the preparation of individualstarting materials of the formula III, are known and described e.g. inU.S. Pat. Nos. 3,384,757 and 3,410,887.

The starting compounds of the formula III are known or they are preparedby methods which are known per se.

Some of the compounds of formula II, wherein W is NH₂, are known. Thenovel compounds of formula II have been specially developed forsynthesising the compounds of formula I. They therefore constitute anobject of the invention.

The starting compounds of formula II, wherein W is --NH--CZ--OR, arenovel and have been specially developed for synthesising the compoundsof formula I. They therefore also constitute an object of the invention.They are prepared by methods which are known per se.

The sulfonamides of the formula II can be prepared by reacting thecorresponding sulfonyl chlorides or sulfonyl fluorides with ammonia orammonium hydroxide solutions (see e.g. J. Chem. Soc. Perkin Trans. 1,1972, 522).

The isocyanates of the formulae II and III can be prepared byphosgenating the corresponding amino compounds, in the presence ofbutylisocyanate and in a chlorinated hydrocarbon as solvent, at refluxtemperature. Reference is made in this connection to "Neuere Methodender praparativen organischen Chemie," Vol. VI, pp. 211-229; VerlagChemie, Weinheim, 1970. When using thiophosgene, isothiocyanates of theformulae II and III are obtained in corresponding manner.

The isothiocyanates of formula II are also prepared by treating thesulfonamides of formula II with carbon disulfide and potassium hydroxideand subsequently phosgenating the dipotassium salt [see Arch. Pharm.299, 174 (1966)].

Compounds of the formulae II and III, wherein W and X are the --NR₁--CZ--OR group, can be obtained from the corresponding amino compoundsby reaction with a haloformate or halothioformate of the formula IV##STR4## or with a dicarbonate or dithiocarbonate of the formula V##STR5## wherein Hal is halogen, preferably chlorine or bromine, Z isoxygen or sulfur and R is an aliphatic or aromatic radical, preferablyC₁ -C₄ alkyl, phenyl or benzyl. This reaction is preferably conducted inthe presence of a base.

The starting amines of the formula III are known or they can be preparedby per se known methods of synthesising heterocyclic amines (see "TheChemistry of Heterocyclic Compounds", Vol. XVI, Interscience Publishers,New York, London, in which methods of synthesising 2-aminopyridines andof 2-amino-1,3,5-triazines may be found).

These reactions are conveniently carried out in aprotic, inert organicsolvents such as methylene chloride, tetrahydrofuran, acetonitrile,dioxan, or toluene.

The reaction temperatures are preferably in the range from -20° to +120°C. The reactions are normally slightly exothermic and can be carried outat room temperature. To shorten the reaction time or also to initiatethe reaction it is expedient to heat the reaction mixture briefly toboiling point. The reaction times can also be shortened by addition of afew drops of a base or isocyanate as catalyst.

The compounds of formula I are stable compounds which are of lowtoxicity to man and animals.

When preparing the compounds of formula I in accordance with equation[1], isomeric reaction products of the formulae Ia and Ib ##STR6## canbe isolated in certain cases by addition of a compound of formula II toa ring nitrogen atom of a compound of formula III. In the formulae Iaand Ib above, R₁, R₂, R₃, Q, Z and E are as defined for formula I. Theseisomeric compounds Ia and Ib also influence plant growth. Accordingly,all agrochemically useful compounds and compound mixtures which areobtained by reacting compounds of formula II with compounds of formulaIII also fall within the province of the present invention.Sulfonylureas containing two to three nitrogen atoms in the 6-memberedheterocyclic radicals Q are novel.

Surprisingly, it has been found that the novel compounds of formula Ihave good selective herbicidal properties and are therefore suitable foruse in crops of cultivated plants. Moreover, it can also be observedthat some of the compounds even damage problem weeds which up to nowhave only been controlled with total herbicides.

A number of the compounds of formula I are translocatable, i.e. they areabsorbed at the treated site of the plant (leaf, stem, root, etc.) andtransported to other sites where they exert their action. In doing so,they not only follow the path of nutrient transport from the roots tothe leaves, but also conversely penetrate to the roots from the leaves.Thus with the aid of this translocatability, e.g. by means of a surfacetreatment, it is possible to damage perennial weeds to their roots.Furthermore, compared with conventional herbicides, the compounds offormula I are effective even when used in very low rates of application.

In addition, the compounds of formula I are able to potentiate thephytotoxic action of other herbicides against certain noxious plants andto reduce the toxicity of such herbicides to some cultivated plants.This can lead to a lowering of the total concentration of herbicide andconsequently to a reduced environmental impact.

If the rates of application are further lowered, then the growthregulating properties of the compounds of formula I predominate. Thecompounds exert a selective action on the plant metabolism, whichresults in particular in a reduction of the vegetative growth often infavour of the generative growth. This selective influence on thephysiological processes of plant development makes the compound offormula I useful for different purposes, especially for those inconnection with labour-saving in measures taken in crops of cultivatedplants or for increasing yield.

The compounds of formula I disclosed herein can be used as herbicidesand/or as growth regulators. Previous experience with growth regulatorshas shown that the active ingredients are able to induce one or moredifferent responses in the plants. These different responses dependlargely on the time of application, i.e. on the development stage of theseed or plant, on the mode of application, and in particular on theconcentrations employed. Such responses differ in turn, however,depending on the species of plant. Accordingly, the application ofcompounds of formula I affords the possibility of influencing the growthof plants in the desired manner.

Vegetative plant growth is inhibited with the novel compounds of theformula I or with the compositions containing them. By means of thisgrowth inhibition the compounds of the invention are able to increasesubstantially the yield of plants. Thus the vegetative growth of e.g.soybean plants and other leguminosae such as beans, peas or lentils isreduced in favour of the generative growth, whereby a direct increase inyield is achieved. The vegetative growth of other species of plants,e.g. of vines, cereals, grasses and ornamentals, is also inhibited indesired manner. In addition, a significant strengthening of thesupporting tissue of the treated plants is observed.

An interesting manner of influencing plant growth derives from thespecial property of the compounds of formula I of selectivelyinfluencing the growth of specific plants, especially cereals. Thisselective growth inhibition substantially increases the breakingstrength of the plants while the yield remains unchanged, therebyproviding a very interesting method of protecting plant crops fromlodging caused by storms or prolonged rainfall. Further, selectiveinhibition of the vegetative growth of many cultivated plants permitsmore plants to be grown per unit of crop area, resulting in asignificant increase in yield with the same fruit setting and in thesame crop area. The use of growth inhibitors also brings about a moreeffective utilisation of nutrients which are then able increasingly topromote flower formation and fruiting. In this manner, higher yields areachieved while the amount of waste vegetative plant residues (e.g.straw, potato foliage, beet leaves) is simultaneously reduced.

To be singled out for special mention is also the possibility ofinhibiting the formation of shoots in different types of plants,especially tobacco plants, whenever the main shoot has been prunedshortly before flowering with the object of increasing the growth of theleaves.

Accordingly, the present invention relates to the use of the compoundsof formula I as herbicides and/or growth regulators. The invention alsorelates to a method of controlling weeds pre- and postemergence, ofinhibiting the growth of monocot and dicot plants, especially ofgrasses, cereals and tobacco suckers, as well as of increasing the yieldof leguminous plants.

The compounds of the formula I are used in unmodified form, orpreferably, together with the adjuvants conventionally employed in theart of formulation, and are therefore formulated in known manner toemulsifiable concentrates, coatable pastes, directly sprayable ordilutable solutions, dilute emulsions, wettable powders, solublepowders, dusts, granulates, and also encapsulations in e.g. polymersubstances. Like the nature of the compositions, the methods ofapplication, such as spraying, atomising, dusting, scattering orpouring, are chosen in accordance with the intended objectives and theprevailing circumstances.

The formulations, i.e. the compositions or preparations containing thecompound (active ingredient) of the formula I and, where appropriate, asolid or liquid adjuvant, are prepared in known manner, e.g. byhomogeneously mixing and/or grinding the active ingredients withextenders, e.g. solvents, solid carriers and, where appropriate,surface-active compounds (surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably the fractionscontaining 8 to 12 carbon atoms, e.g. xylene mixtures or substitutednaphthalenes, phthalates such as dibutyl phthalate or dioctyl phthalate,aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols andglycols and their ethers and esters, such as ethanol, ethylene glycolmonomethyl or monoethyl ether, ketones such as cyclohexanone, stronglypolar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide ordimethyl formamide, as well as epoxidised vegetable oils such asepoxidised coconut oil or soybean oil; or water.

The solid carriers used e.g. for dusts and dispersible powders, arenormally natural mineral fillers such as calcite, talcum, kaolin,montmorillonite or attapulgite. In order to improve the physicalproperties it is also possible to add highly dispersed silicic acid orhighly dispersed absorbent polymers. Suitable granulated adsorptivecarriers are porous types, for example pumice, broken brick, sepioliteor bentonite; and suitable nonsorbent carriers are materials such ascalcite or sand. In addition, a great number of pregranulated materialsof inorganic or organic nature can be used. e.g. especially dolomite orpulverised plant residues.

Depending on the nature of the compound of the formula I to beformulated, suitable surface-active compounds are nonionic, cationicand/or anionic surfactants having good emulsifying, dispersing andwetting properties. The term "surfactants" will also be understood ascomprising mixtures of surfactants.

Suitable anionic surfactants can be both water-soluble soaps andwater-soluble synthetic surface-active compounds.

Suitable soaps are the alkali metal salts, alkaline earth metal salts orunsubstituted or substituted ammonium salts of higher fatty acids (C₁₀-C₂₂), e.g. the sodium or potassium salts of oleic or stearic acid, orof natural fatty acid mixtures which can be obtained e.g. from coconutoil or tallow oil. Mention may also be made of fatty acid methyltaurinsalts.

More frequently, however, so-called synthetic surfactants are used,especially fatty sulfonates, fatty sulfates, sulfonated benzimidazolederivatives or alkylarylsulfonates.

The fatty sulfonates or sulfates are usually in the form of alkali metalsalts, alkaline earth metal salts or unsubstituted or substitutedammoniums salts and contain a C₈ -C₂₂ alkyl radical which also includesthe alkyl moiety of acyl radicals, e.g. the sodium or calcium salt oflignonsulfonic acid, of dodecylsulfate or of a mixture of fatty alcoholsulfates obtained from natural fatty acids. These compounds alsocomprise the salts of sulfuric acid esters and sulfonic acids of fattyalcohol/ethylene oxide adducts. The sulfonated benzimidazole derivativespreferably contain 2 sulfonic acid groups and one fatty acid radicalcontaining 8 to 22 carbon atoms. Examples of alkylarylsulfonates are thesodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid,dibutylnaphthalenesulfonic acid, or of a naphthalenesulfonicacid/formaldehyde condensation product. Also suitable are correspondingphosphates, e.g. salts of the phosphoric acid ester of an adduct ofp-nonylphenol with 4 to 14 moles of ethylene oxide, or phospholipids.

Non-ionic surfactants are preferably polyglycol ether derivatives ofaliphatic or cycloaliphatic alcohols, or saturated or unsaturated fattyacids and alkylphenols, said derivatives containing 3 to 30 glycol ethergroups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moietyand 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.

Further suitable non-ionic surfactants are the water-soluble adducts ofpolyethylene oxide with polypropylene glycol, ethylenediamine propyleneglycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms inthe alkyl chain, which adducts contain 20 to 250 ethylene glycol ethergroups and 10 to 100 propylene glycol ether groups. These compoundsusually contain 1 to 5 ethylene glycol units per propylene glycol unit.

Representative examples of non-ionic surfactants arenonylphenolpolyethoxyethanols, castor oil polyglycol ethers,polypropylene/polyethylene oxide adducts,tributylphenoxypolyethoxyethanol, polyethylene glycol andoctylphenoxyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitanand polyoxyethylene sorbitan trioleate are also suitable non-ionicsurfactants.

Cationic surfactants are preferably quaternary ammonium salts whichcontain, as N-substituent, at least one C₈ -C₂₂ alkyl radical and, asfurther substituents, lower unsubstituted or halogenated alkyl, benzylor lower hydroxyalkyl radicals. The salts are preferably in the form ofhalides, methylsulfates or ethylsulfates, e.g. stearyltrimethylammoniumchloride or benzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants customarily employed in the art of formulation aredescribed e.g. in "McCutcheon's Detergents and Emulsifiers Annual", MCPublishing Corp. Ridgewood, N.J., 1979. and Sisley and Wood,"Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc.New York, 1964.

The pesticidal compositions usually contain 0.1 to 95%, preferably 0.1to 80%, of a compound of the formula I, 1 to 99.9% of a solid or liquidadjuvant, and 0 to 25%, preferably 0.1 to 25%, of a surfactant.

Preferred formulations are composed in particular of the followingconstituents (%=percentage by weight):

Emulsifiable concentrates

active ingredient: 1 to 20%, preferably 5 to 10%

surfactant: 5 to 30%, preferably 10 to 20%

liquid carrier: 50 to 94%, preferably 70 to 85%

Dusts

active ingredient: 0.1 to 10%, preferably 0.1 to 1%

solid carrier: 99.9 to 90%, preferably 99.9 to 99%

Suspension concentrates

active ingredient: 5 to 75%, preferably 10 to 50%

water: 94 to 25%, preferably 90 to 30%

surfactant: 1 to 40%, preferably 2 to 30%

Wettable powders:

active ingredient: 0.5 to 90%, preferably 10 to 80%

surfactant: 0.5 to 20%, preferably 1 to 15%

solid carrier: 5 to 95%, preferably 15 to 90%

Granulates

active ingredient: 0.5 to 30%, preferably 3 to 15%

solid carrier: 99.5 to 70%, preferably 97 to 85%.

Whereas commercial products will be preferably formulated asconcentrates, the end users will normally employ dilute formulations.The formulations can be diluted to a concentration as low as 0.001%. Therates of application are normally from 0.01 to 10 kg a.i./ha.

The compositions may also contain further ingredients, such asstabilisers, antifoams, viscosity regulators, binders, tackifiers aswell as fertilisers or other active ingredients in order to obtainspecial effects.

The invention also relates to agriculturally suitable compositions whichcontain at least one compound of formula I as active ingredient.

Furthermore, the present invention relates to a process for thepreparation of such compositions, which comprises intimately mixing theactive ingredient with one or more substances or groups of substancesdescribed herein. The invention also relates to a method of treatingplants, which comprises applying thereto the compounds of formula I orthe novel compositions containing them.

In the following Examples parts and percentages are by weight.

Preparatory Example Example 1 (a) 3-Chloropyridazine-6-sulfonamide##STR7##

A suspension of 20 g of 3-chloropyridazine-6-thiol and 54.4 g ofpotassium hydrogen fluoride in 200 ml of 50% acetic acid is cooled to 0°C. With vigorous stirring, chlorine is then introduced into thesuspension at 0°-5° C. over 3 hours. The sulfonyl chloride isprecipitated from the reaction mixture by addition of 300 ml of coldwater, isolated by filtration, and washed with cold water. In themeantime, a sulfonating flask is charged with an excess of ammonia. Thesulfonyl chloride is then added, in portions, with stirring. Thereaction mixture is stirred for several hours, diluted with 100 ml ofcold water, and insoluble constituents are removed by filtration. Thefiltrate is adjusted to pH 4 with dilute hydrochloric acid and thenfiltered, affording 11 g of the compound of the above formula with amelting point of 150°-152° C. (decomposition).

(b) N-(3-Chloropyridazine-6-sulfonyl)phenylcarbamate ##STR8##

To a solution of 10.6 g of 3-chloropyridazine-6-sulfonamide in 50 ml ofdimethylformamide are added, under nitrogen and at room temperature, 2.5g of a 55% dispersion of sodium hydride in oil in portions over 15minutes. After a further 15 minutes at 35° C., the reaction mixture iscooled to 25° C. and then 12.4 g of diphenyl carbonate are added to thesolution. The reaction mixture is stirred for 2 hours at roomtemperature and then poured into a mixture of 500 ml of ice/water and 50ml of hydrochloric acid. The precipitate is filtered with suction,washed with cold water and dried in a vacuum cabinet, affording 14.4 gof the compound of the above formula with a melting point of 136° C.

(c)N-(3-Chloropyridazine-6-sulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea##STR9##

A mixture of 14.2 g of N-(3-chloropyridazine-6-sulfonyl)phenylcarbamateand 6.3 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine are refluxed for1 hour in 120 ml of absolute dioxan. When the reaction is complete, themixture is concentrated in vacuo and the residue is taken up in asaturated aqueous solution of sodium bicarbonate and the insolubleconstituents are extracted with methylene chloride. The aqueous phase isacidified with dilute hydrochloric acid and extracted with methylenechloride. The methylene chloride solution is dried over sodium sulfateand concentrated, affording 7 g of the compound of the above formulawith a melting point of 135° C.

The intermediates and final products listed in the following tables canbe prepared in corresponding manner:

                  TABLE 1                                                         ______________________________________                                        QSO.sub.2NH.sub.2                                                             Com-                                                                          pound Q               Abbreviation                                                                             Physical data                                ______________________________________                                        1.1                                                                                  ##STR10##      Q 1        m.p. 109-110° C.                      1.2                                                                                  ##STR11##      Q 2        m.p. 115-120° C.                      1.3                                                                                  ##STR12##      Q 3                                                     1.4                                                                                  ##STR13##      Q 4                                                     1.5                                                                                  ##STR14##      Q 5                                                     1.6                                                                                  ##STR15##      Q 6                                                     1.7                                                                                  ##STR16##      Q 7                                                     1.8                                                                                  ##STR17##      Q 8                                                     1.9                                                                                  ##STR18##      Q 9                                                     1.10                                                                                 ##STR19##      Q 10                                                    1.11                                                                                 ##STR20##      Q 11                                                    1.12                                                                                 ##STR21##      Q 12                                                    1.13                                                                                 ##STR22##      Q 13                                                    1.14                                                                                 ##STR23##      Q 14                                                    1.15                                                                                 ##STR24##      Q 15                                                    1.16                                                                                 ##STR25##      Q 16                                                    1.17                                                                                 ##STR26##      Q 17                                                    1.18                                                                                 ##STR27##      Q 18                                                    1.19                                                                                 ##STR28##      Q 19                                                    1.20                                                                                 ##STR29##      Q 20                                                    1.21                                                                                 ##STR30##      Q 21                                                    1.22                                                                                 ##STR31##      Q 22                                                    1.23                                                                                 ##STR32##      Q 23                                                    1.24                                                                                 ##STR33##      Q 24                                                    1.25                                                                                 ##STR34##      Q 25                                                    1.26                                                                                 ##STR35##      Q 26                                                    1.27                                                                                 ##STR36##      Q 27                                                    1.28                                                                                 ##STR37##      Q 28                                                    1.29                                                                                 ##STR38##      Q 29                                                    1.30                                                                                 ##STR39##      Q 30                                                    1.31                                                                                 ##STR40##      Q 31                                                    1.32                                                                                 ##STR41##      Q 32                                                    1.33                                                                                 ##STR42##      Q 33                                                    1.34                                                                                 ##STR43##      Q 34                                                    1.35                                                                                 ##STR44##      Q 35                                                    1.36                                                                                 ##STR45##      Q 36                                                    1.37                                                                                 ##STR46##      Q 37                                                    1.38                                                                                 ##STR47##      Q 38                                                    1.39                                                                                 ##STR48##      Q 39                                                    ______________________________________                                    

                  TABLE 2:                                                        ______________________________________                                        Q-- SO.sub.2 --W                                                              Compound                                                                              Q      W                Physical data                                 ______________________________________                                        2.1     Q 1    --NH--CO--OCH.sub.3                                            2.2     Q 2    --NH--CO--OCH.sub.3                                            2.3     Q 3    --NH--CO--OCH.sub.3                                            2.4     Q 4    --NH--CO--OCH.sub.3                                            2.5     Q 5    --NH--CO--OCH.sub.3                                            2.6     Q 6    --NH--CO--OCH.sub.3                                            2.7     Q 7    --NH--CO--OCH.sub.3                                            2.8     Q 8    --NH--CO--OCH.sub.3                                            2.9     Q 9    --NH--CO--OCH.sub.3                                            2.10    Q 10   --NH--CO--OCH.sub.3                                            2.11    Q 11   --NH--CO--OCH.sub.3                                            2.12    Q 12   --NH--CO--OCH.sub.3                                            2.13    Q 13   --NH--CO--OCH.sub.3                                            2.14    Q 14   --NH--CO--OCH.sub.3                                            2.15    Q 15   --NH--CO--OCH.sub.3                                            2.16    Q 16   --NH--CO--OCH.sub.3                                            2.17    Q 17   --NH--CO--OCH.sub.3                                            2.18    Q 18   --NH--CO--OCH.sub.3                                            2.19    Q 19   --NH--CO--OCH.sub.3                                            2.20    Q 20   --NH--CO--OCH.sub.3                                            2.21    Q 21   --NH--CO--OCH.sub.3                                            2.22    Q 22   --NH--CO--OCH.sub. 3                                           2.23    Q 23   --NH--CO--OCH.sub.3                                            2.24    Q 24   --NH--CO--OCH.sub.3                                            2.25    Q 25   --NH--CO--OCH.sub.3                                            2.26    Q 26   --NH--CO--OCH.sub.3                                            2.27    Q 27   --NH--CO--OCH.sub.3                                            2.28    Q 1    --NH--CO--O--C.sub.6 H.sub.5                                                                   m.p. 141-143° C.                       2.29    Q 2    --NH--CO--O--C.sub.6 H.sub.5                                                                   m.p. 135-136° C.                       2.30    Q 3    --NH--CO--O--C.sub.6 H.sub.5                                   2.31    Q 4    --NH--CO--O--C.sub.6 H.sub.5                                   2.32    Q 5    --NH--CO--O--C.sub.6 H.sub.5                                   2.33    Q 6    --NH--CO--O--C.sub.6 H.sub.5                                   2.34    Q 7    --NH--CO--O--C.sub.6 H.sub.5                                   2.35    Q 8    --NH--CO--O--C.sub.6 H.sub.5                                   2.36    Q 9    --NH--CO--O--C.sub.6 H.sub.5                                   2.37    Q 10   --NH--CO--O--C.sub.6 H.sub.5                                   2.38    Q 11   --NH--CO--O--C.sub.6 H.sub.5                                   2.39    Q 12   --NH--CO--O--C.sub.6 H.sub.5                                   2.40    Q 13   --NH--CO--O--C.sub.6 H.sub.5                                   2.41    Q 14   --NH--CO-- O--C.sub.6 H.sub.5                                  2.42    Q 15   --NH--CO--O--C.sub.6 H.sub.5                                   2.43    Q 16   --NH--CO--O--C.sub.6 H.sub.5                                   2.44    Q 17   --NH--CO--O--C.sub.6 H.sub.5                                   2.45    Q 18   --NH--CO--O--C.sub.6 H.sub.5                                   2.46    Q 19   --NH--CO--O--C.sub.6 H.sub.5                                   2.47    Q 20   --NH--CO--O--C.sub.6 H.sub.5                                   2.48    Q 21   --NH--CO--O--C.sub.6 H.sub.5                                   2.49    Q 22   --NH--CO--O--C.sub.6 H.sub.5                                   2.50    Q 23   --NH--CO--O--C.sub.6 H.sub.5                                   2.51    Q 24   --NH--CO--O--C.sub.6 H.sub.5                                   2.52    Q 25   --NH--CO--O--C.sub.6 H.sub.5                                   2.53    Q 26   --NH--CO--O--C.sub.6 H.sub.5                                   2.54    Q 27   --NH--CO--O--C.sub.6 H.sub.5                                   2.55    Q 1    --NH--CO--OC.sub.2 H.sub.5                                     2.56    Q 2    --NH--CO--OC.sub.2 H.sub.5                                     2.57    Q 3    --NH--CO--OC.sub.2 H.sub.5                                     2.58    Q 4    --NH--CO--OC.sub.2 H.sub.5                                     2.59    Q 5    --NH--CO--OC.sub.2 H.sub.5                                     2.60    Q 6    --NH--CO--OC.sub.2 H.sub.5                                     2.61    Q 7    --NH--CO--OC.sub.2 H.sub.5                                     2.62    Q 8    --NH--CO--OC.sub.2 H.sub.5                                     2.63    Q 9    --NH--CO--OC.sub.2 H.sub.5                                     2.64    Q 10   --NH--CO--OC.sub.2 H.sub.5                                     2.65    Q 11   --NH--CO--OC.sub.2 H.sub.5                                     2.66    Q 12   --NH--CO--OC.sub.2 H.sub.5                                     2.67    Q 13   --NH--CO--OC.sub.2 H.sub.5                                     2.68    Q 14   --NH--CO--OC.sub.2 H.sub.5                                     2.69    Q 15   --NH--CO--OC.sub.2 H.sub.5                                     2.70    Q 16   --NH--CO--OC.sub.2 H.sub.5                                     2.71    Q 17   --NH--CO--OC.sub.2 H.sub.5                                     2.72    Q 18   --NH--CO--OC.sub.2 H.sub.5                                     2.73    Q 19   --NH--CO--OC.sub.2 H.sub.5                                     2.74    Q 20   --NH--CO--OC.sub.2 H.sub.5                                     2.75    Q 21   --NH--CO--OC.sub.2 H.sub.5                                     2.76    Q 22   --NH--CO--OC.sub.2 H.sub.5                                     2.77    Q 23   --NH--CO--OC.sub.2 H.sub.5                                     2.78    Q 24   --NH--CO--OC.sub.2 H.sub.5                                     2.79    Q 25   --NH--CO--OC.sub.2 H.sub.5                                     2.80    Q 26   --NH--CO--OC.sub.2 H.sub.5                                     2.81    Q 27   --NH--CO--OC.sub.2 H.sub.5                                     2.82    Q 28   --NH--CO--OC.sub.2 H.sub.5                                     2.83    Q 1    --N═C═O                                                2.84    Q 2    --N═C═O                                                2.85    Q 3    --N═C═O                                                2.86    Q 4    --N═C═O                                                2.87    Q 5    --N═C═O                                                2.88    Q 6    --N═C═O                                                2.89    Q 8    --N═C═O                                                2.90    Q 9    --N═C═O                                                2.91    Q 10   --N═C═O                                                2.92    Q 11   --N═C═O                                                2.93    Q 12   --N═C═O                                                2.94    Q 13   --N═C═O                                                2.95    Q 14   --N═C═O                                                2.96    Q 15   --N═C═O                                                2.97    Q 16   --N═C═O                                                2.98    Q 17   --N═C═O                                                2.99    Q 18   --N═C═O                                                2.100   Q 19   --N═C═O                                                2.101   Q 20   --N═C═O                                                2.102   Q 21   --N═C═O                                                2.103   Q 22   --N═C═O                                                2.104   Q 23   --N═C═O                                                2.105   Q 24   --N═C═O                                                2.106   Q 25   --N═C═O                                                2.107   Q 26   -- N═C═O                                               2.108   Q 27   --N═C═O                                                ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                         ##STR49##                                                                    Com-                                          m.p.                            pound Q      Z     E    R.sub.1                                                                            R.sub.2                                                                              R.sub.3   [°C.]                    ______________________________________                                        3.1   Q 3    O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.2   Q 3    O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.3   Q 4    O     N    H    OCH.sub.3                                                                            OCH.sub.3                                 3.4   Q 5    S     N    CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                  3.5   Q 7    O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.6   Q 6    O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.7   Q 8    O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.8   Q 8    O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.9   Q 9    O     N    CH.sub.3                                                                           CH.sub.3                                                                             OCH.sub.3                                 3.10  Q 10   O     N    H    CH.sub.3                                                                             OCH.sub. 3                                3.11  Q 10   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.12  Q 11   O     N    H    OCH.sub.3                                                                            OCH.sub.3                                 3.13  Q 11   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.14  Q 27   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.15  Q 27   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.16  Q 13   S     N    H    CH.sub.3                                                                             CH.sub.2                                  3.17  Q 13   O     CH   H    H      H                                         3.18  Q 18   O     N    H    OCH.sub.3                                                                            OCH.sub.3                                 3.19  Q 19   O     N    CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                  3.20  Q 18   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.21  Q 3    O     CH   H    CH.sub.3                                                                             CH.sub.3  160-                                                                          161                             3.22  Q 3    O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.23  Q 5    O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.24  Q 5    O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.25  Q 6    O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.26  Q 17   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.27  Q 17   O     N    H    OCH.sub.3                                                                            OCH.sub.3                                 3.28  Q 6    O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.29  Q 20   O     N    CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                  3.30  Q 7    S     N    H    CH.sub.3                                                                             OC.sub.3 H.sub.7n                         3.31  Q 21   O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.32  Q 13   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.33  Q 13   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.34  Q 22   S     CH   CH.sub.3                                                                           CH.sub.3                                                                             CH.sub.3                                  3.35  Q 23   O     N    H    OCH.sub.3                                                                            OCH.sub.3                                 3.36  Q 1    O     N    H    CH.sub.3                                                                             OCH.sub.3 153-                                                                          154                             3.37  Q 1    O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                       154-                                                                          155                             3.38  Q 1    O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.39  Q 1    O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.40  Q 1    O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.41  Q 1    O     N    H    C.sub.2 H.sub.5                                                                      OCH.sub.3 139-                                                                          141                             3.42  Q 1    O     N    H    OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          3.43  Q 1    O     N    H    SCH.sub.3                                                                            OCH.sub.3                                 3.44  Q 1    O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                        143-                                                                          144                             3.45  Q 1    O     CH   H    CH.sub.3                                                                             CH.sub.3  165-                                                                          167                             3.46  Q 1    O     CH   H    CH.sub.3                                                                             OCH.sub.3 138-                                                                          141                             3.47  Q 1    O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                                                              142-                                                                          145                             3.48  Q 1    O     CH   H    CH.sub.3                                                                             N(CH.sub.3).sub.2                         3.49  Q 1    O     CH   H    OCH.sub.3                                                                            OCH.sub.3 160-                                                                          163                             3.50  Q 1    O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.51  Q 1    O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.52  Q 1    O     CH   H    OCH.sub.3                                                                            Cl                                        3.53  Q 1    O     CH   H    OCH.sub.3                                                                            F                                         3.54  Q 1    O     CH   H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.55  Q 1    O     CH   H    CH.sub.2 F                                                                           OCH.sub.3                                 3.56  Q 1    O     CH   H    OCHF.sub.2                                                                           N(CH.sub.3).sub.2                         3.57  Q 1    O     CH   H    OCH.sub.3                                                                            OCF.sub.2CHF.sub.2                        3.58  Q 1    O     CH   H    CH.sub.3                                                                             OCF.sub.2CHF.sub.2                        3.59  Q 2    O     N    H    CH.sub.3                                                                             OCH.sub.3 135-                                                                          137                             3.60  Q 2    O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                                                                       180-                                                                          181                             3.61  Q 2    O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.62  Q 2    O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.63  Q 2    O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.64  Q 2    O     N    H    C.sub.2 H.sub.5                                                                      OCH.sub.3 122-                                                                          124                             3.65  Q 2    O     N    H    OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          3.66  Q 2    O     N    H    SCH.sub.3                                                                            OCH.sub.3                                 3.67  Q 2    O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                                                                        123-                                                                          125                             3.68  Q 2    O     CH   H    CH.sub.3                                                                             CH.sub.3  166-                                                                          167                             3.69  Q 2    O     CH   H    CH.sub.3                                                                             OCH.sub.3 139-                                                                          141                             3.70  Q 2    O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                                                              116-                                                                          123                             3.71  Q 2    O     CH   H    CH.sub.3                                                                             N(CH.sub.3).sub.2                         3.72  Q 2    O     CH   H    OCH.sub.3                                                                            OCH.sub.3 143-                                                                          147                             3.73  Q 2    O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.74  Q 2    O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.75  Q 2    O     CH   H    OCH.sub.3                                                                            Cl                                        3.76  Q 2    O     CH   H    OCH.sub.3                                                                            F                                         3.77  Q 2    O     CH   H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.78  Q 2    O     CH   H    CH.sub.2 F                                                                           OCH.sub.3                                 3.79  Q 2    O     CH   H    OCHF.sub.2                                                                           N(CH.sub.3).sub.2                         3.80  Q 2    O     CH   H    OCH.sub.3                                                                            OCF.sub.2CHF.sub.2                        3.81  Q 2    O     CH   H    CH.sub.3                                                                             OCF.sub.2CHF.sub.2                        3.82  Q 14   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.83  Q 14   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.84  Q 14   O     CH   H    CH.sub.3                                                                             CH.sub.3                                  3.85  Q 14   O     CH   H    OCH.sub.3                                                                            OCH.sub.3                                 3.86  Q 14   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.87  Q 24   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.88  Q 24   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.89  Q 24   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.90  Q 25   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.91  Q 25   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.92  Q 26   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.93  Q 26   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.94  Q 15   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.95  Q 15   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.96  Q 15   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.97  Q 16   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.98  Q 16   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.99  Q 17   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.100 Q 17   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.101 Q 27   O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.102 Q 27   O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.103 Q 27   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.104 Q 27   O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.105 Q 27   O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.106 Q 27   O     N    H    C.sub. 2 H.sub.5                                                                     OCH.sub.3                                 3.107 Q 27   O     N    H    OCH.sub.3                                                                            OCH.sub.3                                 3.108 Q 27   O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.109 Q 27   O     CH   H    CH.sub.3                                                                             CH.sub.3                                  3.110 Q 27   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.111 Q 27   O     CH   CH.sub.3                                                                           CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.112 Q 27   O     CH   H    OCH.sub.3                                                                            OCH.sub.3                                 3.113 Q 27   O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.114 Q 27   O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.115 Q 30   O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.116 Q 30   O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.117 Q 30   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.118 Q 30   O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.119 Q 30   O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.120 Q 30   O     N    H    C.sub.2 H.sub.5                                                                      OCH.sub.3                                 3.121 Q 30   O     N    H    OCH.sub.3                                                                            OCH.sub.3                                 3.122 Q 30   O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.123 Q 30   O     CH   H    CH.sub.3                                                                             CH.sub.3                                  3.124 Q 30   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.125 Q 30   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.126 Q 30   O     CH   H    OCH.sub.3                                                                            OCH.sub.3                                 3.127 Q 30   O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.128 Q 30   O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.129 Q 32   O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.130 Q 32   O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.131 Q 32   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.132 Q 32   O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.133 Q 32   O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.134 Q 32   O     N    H    C.sub.2 H.sub.5                                                                      OCH.sub.3                                 3.135 Q 32   O     N    H    OCH.sub.3                                                                            OCH.sub.3                                 3.136 Q 32   O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.137 Q 32   O     CH   H    CH.sub.3                                                                             CH.sub.3                                  3.138 Q 32   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.139 Q 32   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.140 Q 32   O     CH   H    OCH.sub.3                                                                            OCH.sub.3                                 3.141 Q 32   O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.142 Q 32   O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.143 Q 33   O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.144 Q 33   O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.145 Q 33   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.146 Q 33   O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.147 Q 33   O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.148 Q 33   O     N    H    C.sub.2 H.sub.5                                                                      OCH.sub.3                                 3.149 Q 33   O     N    H    OCH.sub.3                                                                            OCH.sub.3                                 3.150 Q 33   O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.151 Q 33   O     CH   H    CH.sub.3                                                                             CH.sub.3                                  3.152 Q 33   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.153 Q 33   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.154 Q 33   O     CH   H    OCH.sub.3                                                                            OCH.sub.3                                 3.155 Q 33   O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.156 Q 33   O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.157 Q 34   O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.158 Q 34   O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.159 Q 34   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.160 Q 34   O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.161 Q 34   O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.162 Q 34   O     N    H    C.sub.2 H.sub.5                                                                      OCH.sub.3                                 3.163 Q 34   O     N    H    OCH.sub.3                                                                            OCH.sub.3                                 3.164 Q 34   O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.165 Q 34   O     CH   H    CH.sub.3                                                                             CH.sub.3                                  3.166 Q 34   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.167 Q 34   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.168 Q 34   O     CH   H    OCH.sub.3                                                                            OCH.sub.3                                 3.169 Q 34   O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.170 Q 34   O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.171 Q 37   O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.172 Q 37   O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.173 Q 37   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.174 Q 37   O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.175 Q 37   O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.176 Q 37   O     N    H    C.sub.2 H.sub.5                                                                      OCH.sub.3                                 3.177 Q 37   O     N    H    OCH.sub.3                                                                            OCH.sub.3                                 3.178 Q 37   O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.179 Q 37   O     CH   H    CH.sub.3                                                                             CH.sub.3                                  3.180 Q 37   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.181 Q 37   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.182 Q 37   O     CH   H    OCH.sub.3                                                                            OCH.sub.3                                 3.183 Q 37   O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.184 Q 37   O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.185 Q 38   O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.186 Q 38   O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.187 Q 38   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.188 Q 38   O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.189 Q 38   O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.190 Q 38   O     N    H    C.sub.2 H.sub.5                                                                      OCH.sub.3                                 3.191 Q 38   O     N    H    OCH.sub.3                                                                            OCH.sub.3                                 3.192 Q 38   O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.193 Q 38   O     CH   H    CH.sub.3                                                                             CH.sub.3                                  3.194 Q 38   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.195 Q 38   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.196 Q 38   O     CH   H    OCH.sub.3                                                                            OCH.sub.3                                 3.197 Q 38   O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.198 Q 38   O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.199 Q 39   O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.200 Q 39   O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.201 Q 39   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.202 Q 39   O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.203 Q 39   O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.204 Q 39   O     N    H    C.sub.2 H.sub.5                                                                      OCH.sub.3                                 3.205 Q 39   O     N    H    OCH.sub.3                                                                            OCH.sub.3                                 3.206 Q 39   O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.207 Q 39   O     CH   H    CH.sub.3                                                                             CH.sub.3                                  3.208 Q 39   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 2.209 Q 39   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.210 Q 39   O     CH   H    OCH.sub.3                                                                            OCH.sub.3                                 3.211 Q 39   O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.212 Q 39   O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.213 Q 28   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.214 Q 28   O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.215 Q 28   O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.216 Q 28   O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.217 Q 28   O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.218 Q 28   O     N    H    C.sub.2 H.sub.5                                                                      OCH.sub.3                                 3.219 Q 28   O     N    H    OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          3.220 Q 28   O     N    H    SCH.sub.3                                                                            OCH.sub.3                                 3.221 Q 28   O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.222 Q 28   O     CH   H    CH.sub.3                                                                             CH.sub.3                                  3.223 Q 28   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.224 Q 28   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.225 Q 28   O     CH   H    CH.sub.3                                                                             N(CH.sub.3).sub.2                         3.226 Q 28   O     CH   H    OCH.sub.3                                                                            OCH.sub.3                                 2.227 Q 28   O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.228 Q 28   O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.229 Q 28   O     CH   H    OCH.sub.3                                                                            Cl                                        3.230 Q 28   O     CH   H    OCH.sub.3                                                                            F                                         3.231 Q 28   O     CH   H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.232 Q 28   O     CH   H    CH.sub.2 F                                                                           OCH.sub.3                                 3.233 Q 28   O     CH   H    OCHF.sub.2                                                                           N(CH.sub.3).sub.2                         3.234 Q 28   O     CH   H    OCH.sub.3                                                                            OCF.sub.2CHF.sub.2                        3.235 Q 28   O     CH   H    CH.sub.3                                                                             OCF.sub.2CHF.sub.2                        3.236 Q 29   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.237 Q 29   O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.238 Q 29   O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.239 Q 29   O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.240 Q 29   O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.241 Q 29   O     N    H    C.sub.2 H.sub.5                                                                      OCH.sub.3                                 3.242 Q 29   O     N    H    OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          3.243 Q 29   O     N    H    SCH.sub.3                                                                            OCH.sub.3                                 3.244 Q 29   O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.245 Q 29   O     CH   H    CH.sub.3                                                                             CH.sub.3                                  3.246 Q 29   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.247 Q 29   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.248 Q 29   O     CH   H    CH.sub.3                                                                             N(CH.sub.3).sub.2                         3.249 Q 29   O     CH   H    OCH.sub.3                                                                            OCH.sub.3                                 3.250 Q 29   O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.251 Q 29   O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.252 Q 29   O     CH   H    OCH.sub.3                                                                            Cl                                        3.253 Q 29   O     CH   H    OCH.sub.3                                                                            F                                         3.254 Q 29   O     CH   H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.255 Q 29   O     CH   H    CH.sub.2 F                                                                           OCH.sub.3                                 3.256 Q 29   O     CH   H    OCHF.sub.2                                                                           N(CH.sub.3).sub.2                         3.257 Q 29   O     CH   H    OCH.sub.3                                                                            OCF.sub.2CHF.sub.2                        3.258 Q 29   O     CH   H    CH.sub.3                                                                             OCF.sub.2CHF.sub.2                        3.259 Q 31   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.260 Q 31   O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.261 Q 31   O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.262 Q 31   O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.263 Q 31   O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.264 Q 31   O     N    H    C.sub.2 H.sub.5                                                                      OCH.sub.3                                 3.265 Q 31   O     N    H    OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          3.266 Q 31   O     N    H    SCH.sub.3                                                                            OCH.sub.3                                 3.267 Q 31   O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.268 Q 31   O     CH   H    CH.sub.3                                                                             CH.sub.3                                  3.269 Q 31   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.270 Q 31   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.271 Q 31   O     CH   H    CH.sub.3                                                                             N(CH.sub.3).sub.2                         3.272 Q 31   O     CH   H    OCH.sub.3                                                                            OCH.sub.3                                 3.273 Q 31   O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.274 Q 31   O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.275 Q 31   O     CH   H    OCH.sub.3                                                                            Cl                                        3.276 Q 31   O     CH   H    OCH.sub.3                                                                            F                                         3.277 Q 31   O     CH   H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.278 Q 31   O     CH   H    CH.sub.2 F                                                                           OCH.sub.3                                 3.279 Q 31   O     CH   H    OCHF.sub.2                                                                           N(CH.sub.3).sub.2                         3.280 Q 31   O     CH   H    OCH.sub.3                                                                            OCF.sub.2CHF.sub.2                        3.281 Q 31   O     CH   H    CH.sub.3                                                                             OCF.sub.2CHF.sub.2                        3.282 Q 35   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.283 Q 35   O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.284 Q 35   O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.285 Q 35   O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.286 Q 35   O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.287 Q 35   O     N    H    C.sub.2 H.sub.5                                                                      OCH.sub.3                                 3.288 Q 35   O     N    H    OC.sub.2 H.sub.5                                                                     OC.sub. 2 H.sub.5                         3.289 Q 35   O     N    H    SCH.sub.3                                                                            OCH.sub.3                                 3.290 Q 35   O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.291 Q 35   O     CH   H    CH.sub.3                                                                             CH.sub.3                                  3.292 Q 35   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.293 Q 35   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.294 Q 35   O     CH   H    CH.sub.3                                                                             N(CH.sub.3).sub.2                         3.295 Q 35   O     CH   H    OCH.sub.3                                                                            OCH.sub.3                                 3.296 Q 35   O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.297 Q 35   O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.298 Q 35   O     CH   H    OCH.sub.3                                                                            Cl                                        3.299 Q 35   O     CH   H    OCH.sub.3                                                                            F                                         3.300 Q 35   O     CH   H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.301 Q 35   O     CH   H    CH.sub.2 F                                                                           OCH.sub.3                                 3.303 Q 35   O     CH   H    OCHF.sub.2                                                                           N(CH.sub.3).sub.2                         3.304 Q 35   O     CH   H    OCH.sub.3                                                                            OCF.sub.2CHF.sub.2                        3.305 Q 35   O     CH   H    CH.sub.3                                                                             OCF.sub.2CHF.sub.2                        3.306 Q 1    O     N    H    OCH.sub.3                                                                            OCH.sub.3 142-                                                                          143                             3.307 Q 2    O     N    H    OCH.sub.3                                                                            OCH.sub.3 124-                                                                          126                             3.308 Q 36   O     N    H    CH.sub.3                                                                             OCH.sub.3                                 3.309 Q 36   O     N    H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.310 Q 36   O     N    H    OCH.sub.3                                                                            OC.sub.2 H.sub.5                          3.311 Q 36   O     N    H    OCH.sub.3                                                                            OCH(CH.sub.3).sub.2                       3.312 Q 36   O     N    H    OCH.sub.3                                                                            OCH.sub.2 CF.sub.3                        3.313 Q 36   O     N    H    C.sub.2 H.sub.5                                                                      OCH.sub.3                                 3.314 Q 36   O     N    H    OC.sub.2 H.sub.5                                                                     OC.sub.2 H.sub.5                          3.315 Q 36   O     N    H    SCH.sub.3                                                                            OCH.sub.3                                 3.316 Q 36   O     N    H    CH.sub.3                                                                             OC.sub.2 H.sub.5                          3.317 Q 36   O     CH   H    CH.sub.3                                                                             CH.sub.3                                  3.318 Q 36   O     CH   H    CH.sub.3                                                                             OCH.sub.3                                 3.319 Q 36   O     CH   H    CH.sub.3                                                                             OCHF.sub.2                                3.320 Q 36   O     CH   H    CH.sub.3                                                                             N(CH.sub.3).sub.2                         3.321 Q 36   O     CH   H    OCH.sub.3                                                                            OCH.sub.3                                 3.322 Q 36   O     CH   H    OCHF.sub.2                                                                           OCHF.sub.2                                3.323 Q 36   O     CH   H    OCH.sub.3                                                                            OCHF.sub.2                                3.324 Q 36   O     CH   H    OCH.sub. 3                                                                           Cl                                        3.325 Q 36   O     CH   H    OCH.sub.3                                                                            F                                         3.326 Q 36   O     CH   H    OCH.sub.3                                                                            N(CH.sub.3).sub.2                         3.327 Q 36   O     CH   H    CH.sub.2 F                                                                           OCH.sub.3                                 3.328 Q 36   O     CH   H    OCHF.sub.2                                                                           N(CH.sub.3).sub.2                         3.329 Q 36   O     CH   H    OCH.sub.3                                                                            OCF.sub.2CHF.sub.2                        3.330 Q 36   O     CH   H    CH.sub.3                                                                             OCF.sub.2CHF.sub.2                        ______________________________________                                    

For application, the compounds of formula I can be processed to thefollowing formulations.

Formulation Examples Example 2

    ______________________________________                                        Formulation examples for compounds of formula I                               (percentages are by weight)                                                   (a) Wettable powders      (a)    (b)  (c)                                     ______________________________________                                        compound of formula I 20%    60%    0.5%                                      sodium lignosulfonate  5%     5%    5%                                        sodium laurylsulfate   3%    --     --                                        sodium diisobutylnaphthalenesulfonate                                                               --      6%    6%                                        octylphenol polyethylene glycol ether                                                               --      2%    2%                                        (7-8 moles of ethylene oxide)                                                 highly dispersed silicic acid                                                                        5%    27%    27%                                       kaolin                67%    --     --                                        sodium chloride       --     --     59.5%                                     ______________________________________                                    

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording wettablepowders which can be diluted with water to give suspensions of thedesired concentration.

    ______________________________________                                        (b) Emulsifiable concentrate   (a)    (b)                                     ______________________________________                                        compound of formula I      10%     1%                                         octylphenol polyethylene glycol ether                                                                     3%     3%                                         (4-5 moles of ethylene oxide)                                                 calcium dodecylbenzenesulfonate castor oil                                                                4%     4%                                         polyglycol ether (36 moles of ethylene oxide)                                 cyclohexanone              30%    10%                                         xylene mixture             50%    79%                                         ______________________________________                                    

Emulsions of any required concentration can be obtained from thisconcentrate by dilution with water.

    ______________________________________                                        (c)    Dusts             (a)     (b)                                          ______________________________________                                        compound of formula I                                                                               0.1%    1%                                              talcum               99.9%   --                                               kaolin               --      99%                                              ______________________________________                                    

Ready for use dusts are obtained by mixing the active ingredient withthe carriers, and grinding the mixture in a suitable mill.

    ______________________________________                                        (d)    Extruder granulate                                                                              (a)    (b)                                           ______________________________________                                        compound of formula I                                                                              10%    1%                                                sodium lignosulfonate                                                                               2%    2%                                                carboxymethylcellulose                                                                              1%    1%                                                kaolin               87%    96%                                               ______________________________________                                    

The active ingredient is mixed and ground with the adjuvants, and themixture is subsequently moistened with water. The mixture is extrudedand then dried in a stream of air.

    ______________________________________                                        (e)      Coated granulate                                                     ______________________________________                                               compound of formula I                                                                        3%                                                             polyethylene glycol 200                                                                      2%                                                             kaolin        94%                                                      ______________________________________                                    

The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coatedgranulates are obtained in this manner.

    ______________________________________                                        (f) Suspension concentrate  (a)     (b)                                       ______________________________________                                        compound of formula I   40%     5%                                            ethylene glycol         10%     10%                                           nonylphenol polyethylene glycol ether                                                                  6%     1%                                            (15 moles of ethylene oxide)                                                  sodium lignosulfonate   10%     5%                                            carboxymethylcellulose   1%     1%                                            37% aqueous formaldehyde solution                                                                     0.2%    0.2%                                          silicone oil in the form of a 75%                                                                     0.8%    0.8%                                          aqueous emulsion                                                              water                   32%     77%                                           ______________________________________                                    

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspension of anydesired concentration can be obtained by dilution with water.

    ______________________________________                                        (g)    Salt solution                                                          ______________________________________                                        compound of formula       5%                                                  isopropylamine            1%                                                  octylphenol polyethylene glycol ether                                                                   3%                                                  (78 moles of ethylene oxide)                                                  water                    91%                                                  ______________________________________                                    

Emulsions of the desired concentration may be prepared from suchconcentrates by dilution with water. These emulsions are particularlysuitable for foliar application. In addition it is possible to preparefurther wettable powders with other mixture ratios or other carriers andadjuvants customarily employed in formulation technology. The activeingredients are intimately mixed with the adjuvants in suitable mixersand ground in corresponding mills and rollers to give wettable powdersof excellant wettability and suspension power which can in turn bediluted with water to give suspensions of the desired concentrationwhich are particularly suitable for foliar application. The inventionalso relates to such compositions.

Compositions which are formulated in the manner described above andwhich contain one of the compounds of Table 1 can be successfully usedfor growth regulation and/or for herbicidal application.

Biological Examples Example 3 Preemergence herbicidal action

In a greenhouse, plant seeds are sown in flower pots of 12-15 cmdiameter. Immediately after sowing, the surface of the soil is treatedwith an aqueous dispersion or solution of the compounds to be tested.Concentrations of 4 kg a.i./ha are employed. The pots are then kept inthe greenhouse at 22°-25° C. and 50-70% relative humidity. The test isevaluated 3 weeks later. The compounds of formula I are very effectivein this test, i.e. the test plants are irreversibly damaged so that theydie or wither.

Example 4 Postemergence herbicidal action (contact action)

A large number of weeds and cultivated plants, both monocots and dicots,are sprayed postemergence in the 4- to 6-leaf stage with an aqueousdispersion of test compound at a rate of application of 4 kg a.i./ha,and then kept at 24°-26° C. and 45-60% relative humidity. The test isevaluated 15 days after treatment. The compounds of formula I have goodherbicidal action in this test.

Example 5 Growth inhibition of cereals

Summar barley (Hordeum vulgare) and summer rye (Secale) are sown insterilised soil in plastic beakers in a greenhouse and watered asrequired. The cereal shoots are treated about 21 days after sowing withan aqueous spray mixture of a compund of the formula I. Theconcentration corresponds to 0.5 and 2.5 kg respectively of activeingredient per hectare. Evaluation of the growth of the cereals is made10 and 21 days after application. A comparison with untreated controlsshows that the growth of cereal plants treated with compounds of theformula I is significantly reduced.

Example 6 Growth inhibition of grasses

Seeds of the grasses Lolium perenne, Poa pratensis, Festuca ovina, andCynodon dactylon are sown in plastic dishes filled with anearth/peat/sand mixture (6:3:1), in a greenhouse, and watered asrequired. The emergent grasses are cut back weekly to a height of 4 cm,and about 50 days after sowing and 1 day after the last cut are sprayedwith an aqueous spray mixture of a compound of the formula I. Theconcentration of test compound corresponds to a rate of application of2.5 kg per hectare. The growth of the grasses is evaluated 10 and 21days after application. The evaluation shows that the compounds of Table1 effect a significant reduction in growth.

What is claimed is:
 1. a compound of the formula

    Q--SO.sub.2 --NH--CZ--OR

wherein Q is a pyrazine group, said group being unsubstituted orsubstituted by halogen, pseudohalogen, nitro, C₁ -C₆ alkyl, C₁ -C₆haloalkyl, C₁ -C₆ alkoxy, C₁ -C₆ alkylthio, C₁ -C₆ haloalkoxy, C₁ -C₆haloalkylthio, amino, C₁ -C₆ alkylamino, di-C₁ -C₆ -alkylamino, C₁ -C₆alkylcarbonylamino, C₁ -C₆ alkylcarbonyl, C₁ -C₆ alkoxycarbonyl, C₁ -C₆alkylthiocarbonyl, carbamoyl, C₁ -C₆ alkylaminocarbonyl, C₁ -C₆dialkylaminocarbonyl, C₁ -C₆ alkylsulfinyl, C₁ -C₆ alkylsulfonyl, C₂ -C₆alkenyloxy, C₂ -C₆ alkynyloxy, or by phenyl, phenoxy or phenylthio,which are unsubstituted or substituted by halogen, nitro, cyano, C₁ -C₆alkyl, C₁ -C₆ alkoxy, C₁ -C₆ haloalkyl or C₁ -C₆ haloalkoxy, or bybenzyl or benzyl substituted by halogen and/or C₁ -C₆ alkyl, Z is oxygenor sulfur and R is C₁ -C₄ alkyl, phenyl or benzyl.
 2. A compound ofclaim 1 wherein Q is unsubstituted or substituted by alkyl, alkoxy orchlorine and Z is oxygen. 3.N-(2-Methoxypyrazin-3-ylsulfonyl)-methylcarbamate, according to claim 2.4. N-(2-Methylpyrazin-3-ylsulfonyl)-phenylcarbamate, according to claim2.
 5. N-(2-Methoxypyrazin-3-ylsulfonyl)-phenylcarbamate, according toclaim
 2. 6. N-(2-Methylpyrazin-3-ylsulfonyl)-ethylcarbamate, accordingto claim
 2. 7. N-(2-Methoxypyrazin-3-ylsulfonyl)-ethylcarbamate,according to claim
 2. 8.N-(2-Methylpyrazin-3-ylsulfonyl)-methylcarbamate, according to claim 2.